2-Aminonicotinic acid → Methyl 2-aminopyridine-3-carboxylate

HRID 602422Notes

Reaction equation

HRID 602422 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:11][Si](C=[N+]=[N-])(C)C>CO.C1COCC1>[CH3:11][O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][CH:9]=[N:10][C:2]=1[NH2:1]

Participants

5

Reactant 2

HCID 729302-Aminonicotinic acidHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 351633Methyl 2-aminopyridine-3-carboxylateYield 78%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred suspension of 2-amino-nicotinic acid (12.15 g, 87.95 mmol) in a mixture of MeOH (175 mL) and THF (500 mL), under nitrogen at room temperature, was added a solution of trimethylsilyldiazomethane (2M in hexane, 50 mL, 99.5 mmol)) dropwise. After completion of the reaction the volatiles were removed in vacuo and the crude product triturated with disisopropyl ether, filtered and dried to give 2-amino-nicotinic acid methyl ester (10.44 g) as a yellow solid.

Workup

  1. customAfter completion of the reaction the volatiles
  2. customwere removed in vacuo
  3. customthe crude product triturated with disisopropyl ether
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-1052b0b407414ce0844dda143c638e09
Source dataset
uspto-grants-2011_03
Patent number
US07906533B2

Reaction notes

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